Kinship ties play an important role in organised crime, but little attention hasbeen paid as yet to criminal families andintergenerational transmission ofdelinquent behaviour as well as criminal‘leadership.’This paper presents theresults of an in-depth study of seven families in the south of the Netherlands that produced a leader of a criminal group in at least one generation. In almost every generation, most male and female members of these families have criminal records, but intergenerational transmission of criminal leadership has so far occurred in only two families. There is a range of risk factors that promote criminal behaviour across generations, but an important explanation is that family members select their partners and friends from their own closed and deviant subcultures, and seem to favour those who have already developed criminal track records. Apart from risk factors at the individual,family and social environment levels, criminal behaviour was also stimulated by the seven families quickly taking advantage of emerging crime markets,particularly ecstasy production and indoor cannabis cultivation from the 1990s onwards.